# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_footnote _publ_author_address K.Baranowska . ; Department of Inorganic Chemistry, Faculty of Chemistry, Gda\'nsk University of Technology 11/12 G. Narutowicz St., 80233 - PL Gda\'nsk, Poland ; N.Piwowarska . ; Department of Inorganic Chemistry, Faculty of Chemistry, Gda\'nsk University of Technology 11/12 G. Narutowicz St., 80233 - PL Gda\'nsk, Poland ; A.Herman . ; Department of Inorganic Chemistry, Faculty of Chemistry, Gda\'nsk University of Technology 11/12 G. Narutowicz St., 80233 - PL Gda\'nsk, Poland ; A.Dolega . ; Department of Inorganic Chemistry, Faculty of Chemistry, Gda\'nsk University of Technology 11/12 G. Narutowicz St., 80233 - PL Gda\'nsk, Poland ; _publ_contact_author_name 'Dr Anna Dolega' _publ_contact_author_email anndoleg@pg.gda.pl _publ_section_title ; Why should cysteine proteinases utilize at least three amino acids to form the active site? The studies on simple model compounds. ; _publ_contact_author_address ; Department of Chemistry Gda\'nsk University of Technology Narutowicza 11/12, PL-80233 Gda\'nsk, Poland ; _publ_contact_author_fax '048 58 3472694' _publ_contact_author_phone '048 58 3472351' _publ_requested_category FO _publ_requested_coeditor_name ? #===END data_kb4_compound_2 _database_code_depnum_ccdc_archive 'CCDC 815862' _audit_creation_date 2008-06-25T10:58:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H27 O3 S Si, C5 H9 N2' _chemical_formula_sum 'C17 H36 N2 O3 S Si' _chemical_formula_weight 376.63 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.0982(7) _cell_length_b 8.9954(6) _cell_length_c 30.8940(18) _cell_angle_alpha 90 _cell_angle_beta 101.433(4) _cell_angle_gamma 90 _cell_volume 4385.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8411 _cell_measurement_theta_min 2.0121 _cell_measurement_theta_max 32.3556 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.274 _exptl_crystal_size_mid 0.245 _exptl_crystal_size_min 0.127 _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_UB_11 -0.0416982350 _diffrn_orient_matrix_UB_12 0.0206127799 _diffrn_orient_matrix_UB_13 -0.0104802678 _diffrn_orient_matrix_UB_21 -0.0163809497 _diffrn_orient_matrix_UB_22 -0.0368514721 _diffrn_orient_matrix_UB_23 0.0168296769 _diffrn_orient_matrix_UB_31 0.0038827698 _diffrn_orient_matrix_UB_32 0.0665226932 _diffrn_orient_matrix_UB_33 0.0125604155 _diffrn_measurement_device 'KM4CCD, Oxford Diffraction' _diffrn_measurement_device_type '4-axis \k geometry diffractometer' _diffrn_measurement_method '\w scans, 0.6 deg width' _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_unetI/netI 0.0457 _diffrn_reflns_number 14329 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4064 _reflns_number_gt 3139 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2006) ; _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+10.5147P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4064 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.089 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1742 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.332 _refine_ls_restrained_S_all 1.332 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.455 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.123 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1800(2) 0.7210(4) 0.07066(12) 0.0238(8) Uani 1 1 d . . . C2 C 0.2629(3) 0.7997(6) 0.08675(16) 0.0462(12) Uani 1 1 d . . . H2A H 0.2973 0.7424 0.1108 0.069 Uiso 1 1 calc R . . H2B H 0.2521 0.8989 0.0975 0.069 Uiso 1 1 calc R . . H2C H 0.2935 0.8088 0.0624 0.069 Uiso 1 1 calc R . . C3 C 0.1943(3) 0.5654(5) 0.05464(14) 0.0340(10) Uani 1 1 d . . . H3A H 0.2298 0.5093 0.0786 0.051 Uiso 1 1 calc R . . H3B H 0.2228 0.5715 0.0294 0.051 Uiso 1 1 calc R . . H3C H 0.1397 0.515 0.0456 0.051 Uiso 1 1 calc R . . C4 C 0.1253(3) 0.8060(5) 0.03334(14) 0.0415(11) Uani 1 1 d . . . H4A H 0.0718 0.7528 0.0235 0.062 Uiso 1 1 calc R . . H4B H 0.1551 0.8148 0.0087 0.062 Uiso 1 1 calc R . . H4C H 0.1137 0.9054 0.0437 0.062 Uiso 1 1 calc R . . C5 C -0.0869(2) 0.7130(4) 0.07299(12) 0.0224(8) Uani 1 1 d . . . C6 C -0.0530(3) 0.5552(4) 0.07096(15) 0.0311(10) Uani 1 1 d . . . H6A H -0.0267 0.5223 0.1008 0.047 Uiso 1 1 calc R . . H6B H -0.0107 0.5537 0.0521 0.047 Uiso 1 1 calc R . . H6C H -0.0998 0.4882 0.0587 0.047 Uiso 1 1 calc R . . C7 C -0.1281(3) 0.7656(5) 0.02711(14) 0.0353(10) Uani 1 1 d . . . H7A H -0.0866 0.7615 0.0078 0.053 Uiso 1 1 calc R . . H7B H -0.1479 0.8681 0.0287 0.053 Uiso 1 1 calc R . . H7C H -0.1763 0.7012 0.0152 0.053 Uiso 1 1 calc R . . C8 C -0.1501(2) 0.7182(5) 0.10366(14) 0.0302(9) Uani 1 1 d . . . H8A H -0.1226 0.6835 0.1331 0.045 Uiso 1 1 calc R . . H8B H -0.1985 0.6539 0.092 0.045 Uiso 1 1 calc R . . H8C H -0.1699 0.8205 0.1057 0.045 Uiso 1 1 calc R . . C9 C 0.0639(2) 1.1142(4) 0.12908(13) 0.0248(9) Uani 1 1 d . . . C10 C 0.1299(3) 1.2241(4) 0.15192(16) 0.0359(10) Uani 1 1 d . . . H10A H 0.1482 1.1957 0.183 0.054 Uiso 1 1 calc R . . H10B H 0.1052 1.324 0.1502 0.054 Uiso 1 1 calc R . . H10C H 0.1787 1.2234 0.1374 0.054 Uiso 1 1 calc R . . C11 C -0.0102(3) 1.1085(5) 0.15292(16) 0.0354(10) Uani 1 1 d . . . H11A H 0.0106 1.0816 0.1839 0.053 Uiso 1 1 calc R . . H11B H -0.0512 1.034 0.1389 0.053 Uiso 1 1 calc R . . H11C H -0.0376 1.2061 0.1513 0.053 Uiso 1 1 calc R . . C12 C 0.0347(3) 1.1562(5) 0.08106(15) 0.0432(12) Uani 1 1 d . . . H12A H 0.0836 1.1592 0.0666 0.065 Uiso 1 1 calc R . . H12B H 0.0077 1.2543 0.0791 0.065 Uiso 1 1 calc R . . H12C H -0.0061 1.0823 0.0664 0.065 Uiso 1 1 calc R . . C13 C 0.2813(2) 0.5022(5) 0.18539(13) 0.0289(9) Uani 1 1 d . . . H13 H 0.2777 0.5291 0.1553 0.035 Uiso 1 1 calc R . . C14 C 0.3447(2) 0.4279(4) 0.21096(13) 0.0261(9) Uani 1 1 d . . . H14 H 0.3948 0.3922 0.2025 0.031 Uiso 1 1 calc R . . C15 C 0.2490(2) 0.4773(4) 0.25117(13) 0.0230(8) Uani 1 1 d . . . C16 C 0.2022(3) 0.4841(5) 0.28812(14) 0.0344(10) Uani 1 1 d . . . H16A H 0.1904 0.5894 0.2941 0.041 Uiso 1 1 calc R . . H16B H 0.2385 0.4429 0.3151 0.041 Uiso 1 1 calc R . . C17 C 0.1197(3) 0.3996(6) 0.27865(17) 0.0473(13) Uani 1 1 d . . . H17A H 0.0917 0.408 0.304 0.071 Uiso 1 1 calc R . . H17B H 0.1309 0.2947 0.2734 0.071 Uiso 1 1 calc R . . H17C H 0.0828 0.4413 0.2524 0.071 Uiso 1 1 calc R . . N1 N 0.22258(19) 0.5321(3) 0.21089(10) 0.0249(7) Uani 1 1 d . . . H1 H 0.1747 0.5803 0.2019 0.03 Uiso 1 1 calc R . . N2 N 0.32365(19) 0.4133(4) 0.25149(10) 0.0259(7) Uani 1 1 d . . . H2 H 0.3548 0.3683 0.2744 0.031 Uiso 1 1 calc R . . O1 O 0.13962(15) 0.7016(3) 0.10814(8) 0.0206(6) Uani 1 1 d . . . O2 O -0.01917(15) 0.8148(3) 0.08859(8) 0.0198(6) Uani 1 1 d . . . O3 O 0.10622(15) 0.9711(3) 0.13116(8) 0.0213(6) Uani 1 1 d . . . Si1 Si 0.06783(6) 0.80159(11) 0.12613(3) 0.0169(3) Uani 1 1 d . . . S1 S 0.04966(5) 0.70945(11) 0.18481(3) 0.0205(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.027(2) 0.0223(19) 0.0005(16) 0.0119(16) 0.0047(17) C2 0.041(3) 0.061(3) 0.043(3) -0.009(2) 0.023(2) -0.025(3) C3 0.044(3) 0.030(2) 0.031(2) -0.0029(18) 0.017(2) 0.007(2) C4 0.053(3) 0.046(3) 0.032(2) 0.014(2) 0.022(2) 0.021(2) C5 0.0162(18) 0.0222(19) 0.027(2) -0.0044(16) -0.0008(15) -0.0003(16) C6 0.025(2) 0.023(2) 0.045(3) -0.0113(18) 0.0063(19) -0.0052(17) C7 0.029(2) 0.042(3) 0.031(2) -0.0045(19) -0.0048(18) 0.0042(19) C8 0.021(2) 0.032(2) 0.038(2) -0.0051(19) 0.0060(17) 0.0011(18) C9 0.028(2) 0.0165(19) 0.030(2) -0.0026(15) 0.0063(17) 0.0002(16) C10 0.035(2) 0.018(2) 0.055(3) -0.0065(19) 0.010(2) -0.0044(18) C11 0.031(2) 0.023(2) 0.055(3) -0.0057(19) 0.016(2) 0.0037(19) C12 0.068(3) 0.023(2) 0.036(3) 0.0042(18) 0.006(2) 0.010(2) C13 0.029(2) 0.033(2) 0.025(2) 0.0047(17) 0.0053(17) -0.0016(18) C14 0.023(2) 0.027(2) 0.029(2) -0.0005(17) 0.0074(17) -0.0006(17) C15 0.0199(19) 0.022(2) 0.0252(19) -0.0006(15) 0.0005(15) -0.0015(16) C16 0.033(2) 0.042(3) 0.030(2) 0.0029(19) 0.0104(18) 0.000(2) C17 0.033(2) 0.063(3) 0.050(3) 0.019(2) 0.016(2) -0.003(2) N1 0.0201(16) 0.0266(17) 0.0256(17) 0.0027(14) -0.0011(13) 0.0017(14) N2 0.0215(17) 0.0305(18) 0.0240(17) 0.0044(14) 0.0007(13) 0.0021(14) O1 0.0211(13) 0.0217(13) 0.0206(13) 0.0018(10) 0.0082(10) 0.0029(11) O2 0.0211(13) 0.0163(13) 0.0208(13) 0.0016(10) 0.0012(10) 0.0015(10) O3 0.0211(13) 0.0174(13) 0.0264(14) -0.0024(10) 0.0069(11) 0.0005(11) Si1 0.0169(5) 0.0165(5) 0.0173(5) -0.0011(4) 0.0035(4) 0.0000(4) S1 0.0185(5) 0.0254(5) 0.0176(4) 0.0020(4) 0.0040(3) -0.0006(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.446(4) . ? C1 C2 1.507(6) . ? C1 C4 1.512(6) . ? C1 C3 1.517(5) . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 O2 1.433(4) . ? C5 C7 1.516(5) . ? C5 C8 1.522(5) . ? C5 C6 1.528(5) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 O3 1.452(4) . ? C9 C12 1.513(6) . ? C9 C10 1.518(5) . ? C9 C11 1.522(6) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.339(5) . ? C13 N1 1.372(5) . ? C13 H13 0.95 . ? C14 N2 1.367(5) . ? C14 H14 0.95 . ? C15 N1 1.327(5) . ? C15 N2 1.331(5) . ? C15 C16 1.488(6) . ? C16 C17 1.508(6) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1 0.88 . ? N2 H2 0.88 . ? O1 Si1 1.646(2) . ? O2 Si1 1.636(2) . ? O3 Si1 1.641(3) . ? Si1 S1 2.0663(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 107.6(3) . . ? O1 C1 C4 112.7(3) . . ? C2 C1 C4 111.0(4) . . ? O1 C1 C3 105.8(3) . . ? C2 C1 C3 111.0(4) . . ? C4 C1 C3 108.7(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C7 106.1(3) . . ? O2 C5 C8 109.2(3) . . ? C7 C5 C8 110.5(3) . . ? O2 C5 C6 110.7(3) . . ? C7 C5 C6 110.2(3) . . ? C8 C5 C6 110.0(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 C12 108.5(3) . . ? O3 C9 C10 106.1(3) . . ? C12 C9 C10 110.3(3) . . ? O3 C9 C11 110.7(3) . . ? C12 C9 C11 111.2(4) . . ? C10 C9 C11 109.9(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 106.9(3) . . ? C14 C13 H13 126.5 . . ? N1 C13 H13 126.5 . . ? C13 C14 N2 106.8(3) . . ? C13 C14 H14 126.6 . . ? N2 C14 H14 126.6 . . ? N1 C15 N2 106.8(3) . . ? N1 C15 C16 126.0(4) . . ? N2 C15 C16 127.3(4) . . ? C15 C16 C17 113.0(4) . . ? C15 C16 H16A 109 . . ? C17 C16 H16A 109 . . ? C15 C16 H16B 109 . . ? C17 C16 H16B 109 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 N1 C13 109.7(3) . . ? C15 N1 H1 125.2 . . ? C13 N1 H1 125.2 . . ? C15 N2 C14 109.8(3) . . ? C15 N2 H2 125.1 . . ? C14 N2 H2 125.1 . . ? C1 O1 Si1 131.4(2) . . ? C5 O2 Si1 132.8(2) . . ? C9 O3 Si1 130.9(2) . . ? O2 Si1 O3 104.64(13) . . ? O2 Si1 O1 111.11(13) . . ? O3 Si1 O1 105.29(13) . . ? O2 Si1 S1 113.64(10) . . ? O3 Si1 S1 113.94(10) . . ? O1 Si1 S1 107.94(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.29 3.171(3) 175.1 . N2 H2 S1 0.88 2.29 3.131(3) 160.8 4_545 # Attachment 'cif-files.cif' data_kb5_compound_1 _database_code_depnum_ccdc_archive 'CCDC 815863' #TrackingRef 'cif-files.cif' _audit_creation_date 2008-07-21T11:11:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H27 O3 S Si, C4 H7 N2' _chemical_formula_sum 'C16 H34 N2 O3 S Si' _chemical_formula_weight 362.6 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8343(4) _cell_length_b 9.05030(10) _cell_length_c 15.8977(6) _cell_angle_alpha 90 _cell_angle_beta 109.061(4) _cell_angle_gamma 90 _cell_volume 2153.31(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14061 _cell_measurement_theta_min 2.2053 _cell_measurement_theta_max 32.3366 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.347 _exptl_crystal_size_mid 0.321 _exptl_crystal_size_min 0.223 _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.22 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_ub_11 0.0106167436 _diffrn_orient_matrix_ub_12 -0.0685306737 _diffrn_orient_matrix_ub_13 -0.0156454377 _diffrn_orient_matrix_ub_21 0.0053293623 _diffrn_orient_matrix_ub_22 0.03596259 _diffrn_orient_matrix_ub_23 -0.0375670502 _diffrn_orient_matrix_ub_31 0.0458431606 _diffrn_orient_matrix_ub_32 0.0117133169 _diffrn_orient_matrix_ub_33 0.0238597209 _diffrn_measurement_device 'KM4CCD, Oxford Diffraction' _diffrn_measurement_device_type '4-axis \k geometry diffractometer' _diffrn_measurement_method '\w scans, 0.75 deg width' _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_unetI/netI 0.0163 _diffrn_reflns_number 16103 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4936 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2006) ; _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.5721P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4936 _refine_ls_number_parameters 236 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.499 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.097 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.84563(10) 0.51658(16) 0.08106(10) 0.0273(3) Uani 1 1 d . . . C2 C 0.78639(13) 0.49105(19) -0.01471(11) 0.0392(4) Uani 1 1 d . . . H2A H 0.7914 0.3878 -0.0311 0.059 Uiso 1 1 calc R . . H2B H 0.8055 0.5561 -0.0544 0.059 Uiso 1 1 calc R . . H2C H 0.7242 0.5128 -0.0203 0.059 Uiso 1 1 calc R . . C3 C 0.83931(12) 0.67673(16) 0.10828(11) 0.0345(3) Uani 1 1 d . . . H3A H 0.878 0.6912 0.1699 0.052 Uiso 1 1 calc R . . H3B H 0.7774 0.6994 0.1034 0.052 Uiso 1 1 calc R . . H3C H 0.8585 0.7425 0.069 0.052 Uiso 1 1 calc R . . C4 C 0.94195(13) 0.4762(2) 0.09185(16) 0.0508(5) Uani 1 1 d . . . H4A H 0.9796 0.4936 0.1536 0.076 Uiso 1 1 calc R . . H4B H 0.9631 0.5374 0.0519 0.076 Uiso 1 1 calc R . . H4C H 0.9452 0.3718 0.077 0.076 Uiso 1 1 calc R . . C5 C 0.86073(9) 0.49830(17) 0.35692(9) 0.0273(3) Uani 1 1 d D . . C6 C 0.8323(5) 0.4137(7) 0.4244(4) 0.0489(13) Uani 0.685(11) 1 d PD A 1 H6A H 0.7838 0.4668 0.437 0.073 Uiso 0.685(11) 1 calc PR A 1 H6B H 0.8831 0.4036 0.4793 0.073 Uiso 0.685(11) 1 calc PR A 1 H6C H 0.8113 0.3154 0.4008 0.073 Uiso 0.685(11) 1 calc PR A 1 C7 C 0.9371(2) 0.4260(5) 0.3319(2) 0.0414(9) Uani 0.685(11) 1 d PD A 1 H7A H 0.9514 0.487 0.2873 0.062 Uiso 0.685(11) 1 calc PR A 1 H7B H 0.9187 0.3274 0.3073 0.062 Uiso 0.685(11) 1 calc PR A 1 H7C H 0.9901 0.4176 0.3851 0.062 Uiso 0.685(11) 1 calc PR A 1 C8 C 0.8901(3) 0.6555(4) 0.3886(3) 0.0333(8) Uani 0.685(11) 1 d PD A 1 H8A H 0.9079 0.7076 0.343 0.05 Uiso 0.685(11) 1 calc PR A 1 H8B H 0.9409 0.6515 0.444 0.05 Uiso 0.685(11) 1 calc PR A 1 H8C H 0.8404 0.7081 0.3992 0.05 Uiso 0.685(11) 1 calc PR A 1 C6A C 0.8360(11) 0.4635(16) 0.4389(8) 0.059(4) Uani 0.315(11) 1 d PD A 2 H6D H 0.8592 0.5411 0.4835 0.088 Uiso 0.315(11) 1 calc PR A 2 H6E H 0.862 0.3682 0.4634 0.088 Uiso 0.315(11) 1 calc PR A 2 H6F H 0.7708 0.4588 0.423 0.088 Uiso 0.315(11) 1 calc PR A 2 C7A C 0.9125(7) 0.3559(14) 0.3520(5) 0.057(3) Uani 0.315(11) 1 d PD A 2 H7D H 0.8729 0.2704 0.3454 0.085 Uiso 0.315(11) 1 calc PR A 2 H7E H 0.9636 0.3455 0.4067 0.085 Uiso 0.315(11) 1 calc PR A 2 H7F H 0.9339 0.3614 0.3007 0.085 Uiso 0.315(11) 1 calc PR A 2 C8A C 0.9133(8) 0.6338(13) 0.3727(9) 0.063(4) Uani 0.315(11) 1 d PD A 2 H8D H 0.8752 0.7176 0.3755 0.095 Uiso 0.315(11) 1 calc PR A 2 H8E H 0.9376 0.6492 0.324 0.095 Uiso 0.315(11) 1 calc PR A 2 H8F H 0.9625 0.6257 0.4291 0.095 Uiso 0.315(11) 1 calc PR A 2 C9 C 0.72735(11) 0.11782(16) 0.17129(10) 0.0310(3) Uani 1 1 d . . . C10 C 0.67546(12) 0.13046(18) 0.07244(11) 0.0374(4) Uani 1 1 d . . . H10A H 0.7059 0.1999 0.0447 0.056 Uiso 1 1 calc R . . H10B H 0.615 0.1664 0.0645 0.056 Uiso 1 1 calc R . . H10C H 0.6721 0.0332 0.0444 0.056 Uiso 1 1 calc R . . C11 C 0.82329(14) 0.06930(19) 0.18591(16) 0.0496(5) Uani 1 1 d . . . H11A H 0.8554 0.0612 0.2499 0.074 Uiso 1 1 calc R . . H11B H 0.853 0.1424 0.1597 0.074 Uiso 1 1 calc R . . H11C H 0.8232 -0.0269 0.1576 0.074 Uiso 1 1 calc R . . C12 C 0.68019(16) 0.00924(19) 0.21463(13) 0.0483(5) Uani 1 1 d . . . H12A H 0.7139 0.0009 0.2782 0.072 Uiso 1 1 calc R . . H12B H 0.6767 -0.0879 0.1864 0.072 Uiso 1 1 calc R . . H12C H 0.6197 0.0451 0.207 0.072 Uiso 1 1 calc R . . C13 C 0.41852(10) 0.2728(2) 0.10441(11) 0.0353(4) Uani 1 1 d . . . H13 H 0.4008 0.2951 0.0427 0.042 Uiso 1 1 calc R . . C14 C 0.37119(11) 0.1973(2) 0.14662(11) 0.0388(4) Uani 1 1 d . . . H14 H 0.3134 0.1561 0.1201 0.047 Uiso 1 1 calc R . . C15 C 0.49849(10) 0.26072(17) 0.24705(10) 0.0288(3) Uani 1 1 d . . . C16 C 0.57085(13) 0.2798(2) 0.33302(12) 0.0471(5) Uani 1 1 d . . . H16A H 0.6201 0.3354 0.3236 0.071 Uiso 0.5 1 calc PR . . H16B H 0.5925 0.1826 0.358 0.071 Uiso 0.5 1 calc PR . . H16C H 0.5479 0.3339 0.3744 0.071 Uiso 0.5 1 calc PR . . H16D H 0.5536 0.2325 0.3804 0.071 Uiso 0.5 1 calc PR . . H16E H 0.5812 0.3854 0.346 0.071 Uiso 0.5 1 calc PR . . H16F H 0.6258 0.234 0.3296 0.071 Uiso 0.5 1 calc PR . . N1 N 0.49745(8) 0.31141(14) 0.16809(9) 0.0296(3) Uani 1 1 d . . . H1 H 0.5408 0.3619 0.1582 0.035 Uiso 1 1 calc R . . N2 N 0.42167(8) 0.19054(14) 0.23494(9) 0.0292(3) Uani 1 1 d . . . H2 H 0.4058 0.1468 0.2769 0.035 Uiso 1 1 calc R . . O1 O 0.81804(6) 0.41606(10) 0.13723(7) 0.0245(2) Uani 1 1 d . A . O2 O 0.78137(6) 0.51931(11) 0.28039(7) 0.0264(2) Uani 1 1 d . A . O3 O 0.72896(7) 0.25719(10) 0.21622(6) 0.0238(2) Uani 1 1 d . A . Si1 Si 0.74254(2) 0.42718(4) 0.18690(2) 0.01764(11) Uani 1 1 d . . . S1 S 0.62440(2) 0.52649(4) 0.11150(2) 0.02132(11) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0311(7) 0.0246(7) 0.0342(8) 0.0015(6) 0.0216(6) -0.0002(5) C2 0.0591(11) 0.0339(8) 0.0326(8) -0.0031(7) 0.0257(8) -0.0029(8) C3 0.0472(9) 0.0246(7) 0.0407(8) -0.0028(6) 0.0264(7) -0.0096(6) C4 0.0374(9) 0.0569(12) 0.0726(14) 0.0091(10) 0.0377(10) 0.0046(8) C5 0.0208(6) 0.0337(7) 0.0227(6) -0.0057(6) 0.0007(5) 0.0023(6) C6 0.040(2) 0.052(3) 0.0405(18) 0.0317(19) -0.0061(17) -0.014(2) C7 0.0245(14) 0.062(2) 0.0331(15) -0.0095(14) 0.0029(11) 0.0152(13) C8 0.0269(19) 0.0351(14) 0.0316(16) -0.0067(11) 0.0008(13) -0.0097(12) C6A 0.032(4) 0.056(8) 0.072(7) 0.033(5) -0.007(4) -0.019(6) C7A 0.034(4) 0.100(8) 0.025(3) -0.016(4) -0.007(3) 0.034(5) C8A 0.033(5) 0.091(8) 0.053(7) 0.031(5) -0.004(4) -0.026(5) C9 0.0436(8) 0.0170(6) 0.0342(8) -0.0016(6) 0.0151(7) -0.0034(6) C10 0.0527(10) 0.0300(8) 0.0317(8) -0.0105(6) 0.0167(7) -0.0103(7) C11 0.0500(11) 0.0245(8) 0.0720(14) -0.0050(8) 0.0170(10) 0.0097(7) C12 0.0762(14) 0.0256(8) 0.0475(10) 0.0025(7) 0.0265(10) -0.0144(8) C13 0.0279(7) 0.0457(9) 0.0323(8) 0.0096(7) 0.0097(6) -0.0006(6) C14 0.0261(7) 0.0511(10) 0.0383(8) 0.0079(8) 0.0093(7) -0.0059(7) C15 0.0289(7) 0.0305(7) 0.0308(7) -0.0001(6) 0.0151(6) -0.0016(6) C16 0.0439(10) 0.0642(12) 0.0324(9) -0.0035(8) 0.0113(8) -0.0144(9) N1 0.0263(6) 0.0340(6) 0.0324(6) 0.0037(5) 0.0150(5) -0.0044(5) N2 0.0299(6) 0.0302(6) 0.0328(6) 0.0051(5) 0.0175(5) -0.0015(5) O1 0.0252(5) 0.0210(5) 0.0322(5) 0.0039(4) 0.0159(4) 0.0032(4) O2 0.0211(5) 0.0288(5) 0.0241(5) -0.0092(4) 0.0004(4) 0.0045(4) O3 0.0330(5) 0.0184(4) 0.0215(5) 0.0004(4) 0.0107(4) -0.0019(4) Si1 0.01858(19) 0.01660(18) 0.01802(18) -0.00123(12) 0.00635(14) -0.00022(12) S1 0.01876(17) 0.02651(19) 0.01914(17) 0.00312(12) 0.00682(13) 0.00143(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4389(16) . ? C1 C4 1.523(2) . ? C1 C2 1.523(2) . ? C1 C3 1.525(2) . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 O2 1.4480(16) . ? C5 C8A 1.457(8) . ? C5 C6 1.501(4) . ? C5 C6A 1.511(9) . ? C5 C8 1.531(4) . ? C5 C7 1.538(3) . ? C5 C7A 1.543(7) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C6A H6D 0.98 . ? C6A H6E 0.98 . ? C6A H6F 0.98 . ? C7A H7D 0.98 . ? C7A H7E 0.98 . ? C7A H7F 0.98 . ? C8A H8D 0.98 . ? C8A H8E 0.98 . ? C8A H8F 0.98 . ? C9 O3 1.4456(17) . ? C9 C10 1.521(2) . ? C9 C11 1.525(3) . ? C9 C12 1.528(2) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.344(2) . ? C13 N1 1.372(2) . ? C13 H13 0.95 . ? C14 N2 1.372(2) . ? C14 H14 0.95 . ? C15 N2 1.3293(19) . ? C15 N1 1.3316(19) . ? C15 C16 1.479(2) . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? C16 H16D 0.98 . ? C16 H16E 0.98 . ? C16 H16F 0.98 . ? N1 H1 0.88 . ? N2 H2 0.88 . ? O1 Si1 1.6369(10) . ? O2 Si1 1.6386(10) . ? O3 Si1 1.6419(10) . ? Si1 S1 2.0688(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 105.93(13) . . ? O1 C1 C2 108.17(12) . . ? C4 C1 C2 110.09(14) . . ? O1 C1 C3 111.31(11) . . ? C4 C1 C3 110.61(14) . . ? C2 C1 C3 110.60(13) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C8A 108.9(5) . . ? O2 C5 C6 106.7(3) . . ? C8A C5 C6 126.5(6) . . ? O2 C5 C6A 110.7(7) . . ? C8A C5 C6A 108.7(7) . . ? O2 C5 C8 104.0(2) . . ? C6 C5 C8 111.6(3) . . ? C6A C5 C8 92.6(5) . . ? O2 C5 C7 112.24(16) . . ? C8A C5 C7 87.1(6) . . ? C6 C5 C7 114.4(4) . . ? C6A C5 C7 125.6(7) . . ? C8 C5 C7 107.5(2) . . ? O2 C5 C7A 113.4(3) . . ? C8A C5 C7A 115.4(6) . . ? C6 C5 C7A 84.2(6) . . ? C6A C5 C7A 99.3(7) . . ? C8 C5 C7A 133.2(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C6A H6D 109.5 . . ? C5 C6A H6E 109.5 . . ? H6D C6A H6E 109.5 . . ? C5 C6A H6F 109.5 . . ? H6D C6A H6F 109.5 . . ? H6E C6A H6F 109.5 . . ? C5 C7A H7D 109.5 . . ? C5 C7A H7E 109.5 . . ? H7D C7A H7E 109.5 . . ? C5 C7A H7F 109.5 . . ? H7D C7A H7F 109.5 . . ? H7E C7A H7F 109.5 . . ? C5 C8A H8D 109.5 . . ? C5 C8A H8E 109.5 . . ? H8D C8A H8E 109.5 . . ? C5 C8A H8F 109.5 . . ? H8D C8A H8F 109.5 . . ? H8E C8A H8F 109.5 . . ? O3 C9 C10 111.18(12) . . ? O3 C9 C11 108.67(13) . . ? C10 C9 C11 110.74(15) . . ? O3 C9 C12 105.71(13) . . ? C10 C9 C12 109.61(14) . . ? C11 C9 C12 110.83(15) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 106.45(14) . . ? C14 C13 H13 126.8 . . ? N1 C13 H13 126.8 . . ? C13 C14 N2 107.46(14) . . ? C13 C14 H14 126.3 . . ? N2 C14 H14 126.3 . . ? N2 C15 N1 107.40(13) . . ? N2 C15 C16 125.85(14) . . ? N1 C15 C16 126.75(14) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C16 H16D 109.5 . . ? H16A C16 H16D 141.1 . . ? H16B C16 H16D 56.3 . . ? H16C C16 H16D 56.3 . . ? C15 C16 H16E 109.5 . . ? H16A C16 H16E 56.3 . . ? H16B C16 H16E 141.1 . . ? H16C C16 H16E 56.3 . . ? H16D C16 H16E 109.5 . . ? C15 C16 H16F 109.5 . . ? H16A C16 H16F 56.3 . . ? H16B C16 H16F 56.3 . . ? H16C C16 H16F 141.1 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? C15 N1 C13 109.62(13) . . ? C15 N1 H1 125.2 . . ? C13 N1 H1 125.2 . . ? C15 N2 C14 109.08(12) . . ? C15 N2 H2 125.5 . . ? C14 N2 H2 125.5 . . ? C1 O1 Si1 132.69(9) . . ? C5 O2 Si1 131.37(9) . . ? C9 O3 Si1 131.31(9) . . ? O1 Si1 O2 110.61(5) . . ? O1 Si1 O3 105.27(5) . . ? O2 Si1 O3 105.34(5) . . ? O1 Si1 S1 114.32(4) . . ? O2 Si1 S1 107.76(4) . . ? O3 Si1 S1 113.21(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.27 3.1337(12) 165.9 . N2 H2 S1 0.88 2.26 3.1400(12) 175.6 2_645 #===END data_kb14_compound_3 _database_code_depnum_ccdc_archive 'CCDC 815864' #TrackingRef 'cif-files.cif' _audit_creation_date 2009-04-21T08:46:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H38 N2 O3 S1 Si1' _chemical_formula_sum 'C18 H38 N2 O3 S Si' _chemical_formula_weight 390.65 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.691(8) _cell_length_b 9.7022(9) _cell_length_c 31.2081(12) _cell_angle_alpha 90 _cell_angle_beta 103.24(5) _cell_angle_gamma 90 _cell_volume 4625(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10081 _cell_measurement_theta_min 2.4821 _cell_measurement_theta_max 28.7937 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1883 _diffrn_orient_matrix_UB_11 0.0001131194 _diffrn_orient_matrix_UB_12 0.0731184065 _diffrn_orient_matrix_UB_13 -0.0021113306 _diffrn_orient_matrix_UB_21 -0.0466229403 _diffrn_orient_matrix_UB_22 0.0000053777 _diffrn_orient_matrix_UB_23 -0.0059056056 _diffrn_orient_matrix_UB_31 -0.0010594156 _diffrn_orient_matrix_UB_32 0.0067926854 _diffrn_orient_matrix_UB_33 0.0225799704 _diffrn_measurement_device 'KM4CCD, Oxford Diffraction' _diffrn_measurement_device_type '4-axis \k geometry diffractometer' _diffrn_measurement_method '\w scans, 0.5 deg width' _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_unetI/netI 0.0273 _diffrn_reflns_number 14809 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 4294 _reflns_number_gt 3776 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2006) ; _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2006) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+6.0037P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4294 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.503 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.062 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.08654(12) 0.8120(2) 0.06120(6) 0.0257(4) Uani 1 1 d . . . C2 C -0.12389(15) 0.7647(2) 0.01371(7) 0.0366(5) Uani 1 1 d . . . H2A H -0.0781 0.7696 -0.0029 0.055 Uiso 1 1 calc R . . H2B H -0.1727 0.8248 -0.0001 0.055 Uiso 1 1 calc R . . H2C H -0.1448 0.6695 0.0138 0.055 Uiso 1 1 calc R . . C3 C -0.04815(14) 0.9569(2) 0.06274(7) 0.0334(5) Uani 1 1 d . . . H3A H -0.0266 0.9851 0.0935 0.05 Uiso 1 1 calc R . . H3B H -0.0936 1.0213 0.048 0.05 Uiso 1 1 calc R . . H3C H 0.0004 0.9573 0.0478 0.05 Uiso 1 1 calc R . . C4 C -0.15788(13) 0.8054(2) 0.08596(7) 0.0312(5) Uani 1 1 d . . . H4A H -0.18 0.7108 0.0854 0.047 Uiso 1 1 calc R . . H4B H -0.2057 0.8673 0.0722 0.047 Uiso 1 1 calc R . . H4C H -0.1346 0.8338 0.1165 0.047 Uiso 1 1 calc R . . C5 C 0.05924(13) 0.4289(2) 0.12489(7) 0.0277(4) Uani 1 1 d . . . C6 C 0.01253(17) 0.3947(2) 0.07693(7) 0.0406(5) Uani 1 1 d . . . H6A H -0.0312 0.4659 0.0657 0.061 Uiso 1 1 calc R . . H6B H -0.0165 0.3049 0.076 0.061 Uiso 1 1 calc R . . H6C H 0.0556 0.3916 0.0586 0.061 Uiso 1 1 calc R . . C7 C 0.12999(16) 0.3208(2) 0.14358(9) 0.0422(6) Uani 1 1 d . . . H7A H 0.1743 0.3204 0.126 0.063 Uiso 1 1 calc R . . H7B H 0.1029 0.2295 0.1425 0.063 Uiso 1 1 calc R . . H7C H 0.1577 0.3439 0.1742 0.063 Uiso 1 1 calc R . . C8 C -0.00724(15) 0.4357(2) 0.15224(7) 0.0352(5) Uani 1 1 d . . . H8A H 0.0215 0.4613 0.1825 0.053 Uiso 1 1 calc R . . H8B H -0.0353 0.3455 0.1523 0.053 Uiso 1 1 calc R . . H8C H -0.0516 0.5049 0.1399 0.053 Uiso 1 1 calc R . . C9 C 0.19760(13) 0.7777(2) 0.07619(6) 0.0281(4) Uani 1 1 d . . . C10 C 0.22512(17) 0.9182(2) 0.06243(8) 0.0406(6) Uani 1 1 d . . . H10A H 0.1733 0.9767 0.0531 0.061 Uiso 1 1 calc R . . H10B H 0.254 0.907 0.0379 0.061 Uiso 1 1 calc R . . H10C H 0.2658 0.9612 0.0874 0.061 Uiso 1 1 calc R . . C11 C 0.13978(16) 0.7041(3) 0.03611(7) 0.0435(6) Uani 1 1 d . . . H11A H 0.1199 0.6156 0.0454 0.065 Uiso 1 1 calc R . . H11B H 0.1738 0.6882 0.0138 0.065 Uiso 1 1 calc R . . H11C H 0.0889 0.7618 0.0236 0.065 Uiso 1 1 calc R . . C12 C 0.27846(15) 0.6920(3) 0.09791(8) 0.0406(5) Uani 1 1 d . . . H12A H 0.3112 0.7401 0.1242 0.061 Uiso 1 1 calc R . . H12B H 0.316 0.6797 0.0771 0.061 Uiso 1 1 calc R . . H12C H 0.2597 0.6017 0.1064 0.061 Uiso 1 1 calc R . . C13 C 0.15763(14) 0.5984(2) 0.29106(7) 0.0308(5) Uani 1 1 d . . . H13 H 0.1051 0.6227 0.2994 0.037 Uiso 1 1 calc R . . C14 C 0.22516(14) 0.5220(2) 0.31537(7) 0.0311(5) Uani 1 1 d . . . H14 H 0.228 0.4839 0.3437 0.037 Uiso 1 1 calc R . . C15 C 0.25850(12) 0.5797(2) 0.25375(6) 0.0236(4) Uani 1 1 d . . . C16 C 0.30886(13) 0.6068(2) 0.22049(6) 0.0272(4) Uani 1 1 d . . . H16 H 0.2679 0.6404 0.1931 0.033 Uiso 1 1 calc R . . C17 C 0.35497(15) 0.4790(2) 0.20937(7) 0.0371(5) Uani 1 1 d . . . H17A H 0.3952 0.4446 0.236 0.056 Uiso 1 1 calc R . . H17B H 0.388 0.5019 0.1872 0.056 Uiso 1 1 calc R . . H17C H 0.3115 0.4078 0.1977 0.056 Uiso 1 1 calc R . . C18 C 0.37630(16) 0.7221(2) 0.23797(8) 0.0408(5) Uani 1 1 d . . . H18A H 0.3457 0.8033 0.2456 0.061 Uiso 1 1 calc R . . H18B H 0.4074 0.7467 0.2152 0.061 Uiso 1 1 calc R . . H18C H 0.4184 0.6891 0.2642 0.061 Uiso 1 1 calc R . . O1 O -0.01831(8) 0.71328(13) 0.08058(4) 0.0247(3) Uani 1 1 d . . . O2 O 0.10615(8) 0.55828(13) 0.12730(4) 0.0246(3) Uani 1 1 d . . . O3 O 0.15032(8) 0.80616(13) 0.10910(4) 0.0241(3) Uani 1 1 d . . . S1 S 0.04930(3) 0.80573(5) 0.178285(14) 0.02266(14) Uani 1 1 d . . . N1 N 0.17953(11) 0.63282(17) 0.25286(6) 0.0263(4) Uani 1 1 d . . . N2 N 0.28713(11) 0.51077(18) 0.29172(5) 0.0264(4) Uani 1 1 d . . . Si1 Si 0.07077(3) 0.71888(5) 0.121910(16) 0.02017(14) Uani 1 1 d . . . H1 H 0.1480(18) 0.681(3) 0.2304(9) 0.050(8) Uiso 1 1 d . . . H2D H 0.3391(17) 0.465(3) 0.2997(8) 0.042(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0224(10) 0.0278(10) 0.0254(10) 0.0011(8) 0.0028(8) 0.0053(8) C2 0.0338(12) 0.0454(13) 0.0270(11) -0.0012(9) -0.0008(9) 0.0067(10) C3 0.0309(11) 0.0299(11) 0.0393(11) 0.0062(9) 0.0082(9) 0.0042(9) C4 0.0243(10) 0.0351(11) 0.0341(11) -0.0014(9) 0.0063(8) 0.0027(9) C5 0.0299(11) 0.0210(10) 0.0336(11) 0.0011(8) 0.0103(9) -0.0006(8) C6 0.0553(15) 0.0287(11) 0.0385(12) -0.0080(9) 0.0119(11) -0.0075(10) C7 0.0417(13) 0.0264(11) 0.0608(15) 0.0102(10) 0.0166(11) 0.0060(10) C8 0.0345(12) 0.0323(12) 0.0417(12) -0.0009(9) 0.0147(10) -0.0072(9) C9 0.0295(11) 0.0321(11) 0.0272(10) -0.0037(8) 0.0159(8) -0.0033(9) C10 0.0512(14) 0.0385(13) 0.0399(12) 0.0017(10) 0.0269(11) -0.0071(11) C11 0.0445(14) 0.0587(16) 0.0335(12) -0.0153(11) 0.0215(11) -0.0117(12) C12 0.0338(12) 0.0430(13) 0.0505(14) -0.0014(11) 0.0213(11) 0.0072(10) C13 0.0281(11) 0.0324(11) 0.0350(11) 0.0029(9) 0.0136(9) 0.0003(9) C14 0.0335(11) 0.0337(11) 0.0282(10) 0.0051(8) 0.0117(9) 0.0000(9) C15 0.0200(9) 0.0253(10) 0.0253(9) 0.0008(7) 0.0045(7) -0.0003(7) C16 0.0216(9) 0.0344(11) 0.0259(10) 0.0054(8) 0.0061(8) 0.0033(8) C17 0.0397(12) 0.0415(13) 0.0342(11) 0.0008(10) 0.0168(10) 0.0080(10) C18 0.0391(13) 0.0412(13) 0.0473(13) 0.0024(10) 0.0209(11) -0.0073(10) O1 0.0235(7) 0.0252(7) 0.0242(7) -0.0021(5) 0.0030(5) 0.0027(5) O2 0.0220(7) 0.0233(7) 0.0296(7) 0.0011(5) 0.0084(5) 0.0007(5) O3 0.0246(7) 0.0260(7) 0.0246(7) -0.0026(5) 0.0116(5) -0.0006(5) S1 0.0199(2) 0.0277(3) 0.0207(2) -0.00222(18) 0.00532(18) 0.00132(18) N1 0.0238(9) 0.0285(9) 0.0270(9) 0.0037(7) 0.0068(7) 0.0027(7) N2 0.0224(9) 0.0287(9) 0.0279(9) 0.0044(7) 0.0053(7) 0.0026(7) Si1 0.0187(3) 0.0221(3) 0.0202(3) -0.00053(19) 0.0054(2) 0.00088(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.460(2) . ? C1 C4 1.500(3) . ? C1 C3 1.526(3) . ? C1 C2 1.534(3) . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 O2 1.449(2) . ? C5 C8 1.493(3) . ? C5 C7 1.541(3) . ? C5 C6 1.544(3) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 O3 1.425(2) . ? C9 C10 1.521(3) . ? C9 C12 1.538(3) . ? C9 C11 1.542(3) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 N1 1.356(3) . ? C13 C14 1.371(3) . ? C13 H13 0.95 . ? C14 N2 1.353(3) . ? C14 H14 0.95 . ? C15 N1 1.336(3) . ? C15 N2 1.345(3) . ? C15 C16 1.465(3) . ? C16 C17 1.515(3) . ? C16 C18 1.551(3) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? O1 Si1 1.6716(17) . ? O2 Si1 1.6497(14) . ? O3 Si1 1.6319(15) . ? S1 Si1 2.0470(7) . ? N1 H1 0.89(3) . ? N2 H2D 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 108.74(16) . . ? O1 C1 C3 110.15(16) . . ? C4 C1 C3 111.03(17) . . ? O1 C1 C2 106.60(16) . . ? C4 C1 C2 108.66(17) . . ? C3 C1 C2 111.52(17) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C8 110.17(16) . . ? O2 C5 C7 104.86(16) . . ? C8 C5 C7 110.55(18) . . ? O2 C5 C6 111.04(16) . . ? C8 C5 C6 108.96(18) . . ? C7 C5 C6 111.22(19) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 C10 104.96(16) . . ? O3 C9 C12 107.46(16) . . ? C10 C9 C12 110.47(19) . . ? O3 C9 C11 111.58(16) . . ? C10 C9 C11 109.76(19) . . ? C12 C9 C11 112.35(19) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 107.47(18) . . ? N1 C13 H13 126.3 . . ? C14 C13 H13 126.3 . . ? N2 C14 C13 107.62(18) . . ? N2 C14 H14 126.2 . . ? C13 C14 H14 126.2 . . ? N1 C15 N2 109.33(17) . . ? N1 C15 C16 124.35(18) . . ? N2 C15 C16 125.99(18) . . ? C15 C16 C17 112.27(17) . . ? C15 C16 C18 108.37(17) . . ? C17 C16 C18 110.34(18) . . ? C15 C16 H16 108.6 . . ? C17 C16 H16 108.6 . . ? C18 C16 H16 108.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 O1 Si1 134.61(12) . . ? C5 O2 Si1 131.17(12) . . ? C9 O3 Si1 129.02(12) . . ? C15 N1 C13 107.89(18) . . ? C15 N1 H1 124.2(18) . . ? C13 N1 H1 127.9(18) . . ? C15 N2 C14 107.67(17) . . ? C15 N2 H2D 125.5(15) . . ? C14 N2 H2D 126.8(15) . . ? O3 Si1 O2 104.88(7) . . ? O3 Si1 O1 112.28(8) . . ? O2 Si1 O1 104.50(7) . . ? O3 Si1 S1 106.41(6) . . ? O2 Si1 S1 114.76(5) . . ? O1 Si1 S1 113.80(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.89(3) 2.31(3) 3.198(2) 171(2) . N2 H2D S1 0.91(3) 2.32(3) 3.213(2) 166(2) 4_545 # END of CIF